Access to pyrrolidine imino sugars via tin(II)-mediated aldol reactions of bislactim ethers: synthesis of 2,5-dideoxy-2,5-imino-D-glucitol.
2,5-Dideoxy-2,5-imino-D-glucitol (DGDP) has been synthesized via the tin(II)-mediated anti-selective aldol reaction of bislactim ether 5 and a 3-O-silylated 2,4-ethylidene-D-erythrose derivative 6. In accordance with density functional theory calculations (at the B3LYP/cc-pVDZ-PP level), pericyclic transition structures with a boat-like conformation and a stabilizing hydrogen bond can account for the unexpected stereoselectivity.
Blanco
Olga
O
Departamento de Química Fundamental, Facultade de Ciencias, Universidade da Coruña, Campus da Zapateira s/n, 15071 A Coruña, Spain.
Pato
Cristina
C
Ruiz
María
M
Ojea
Vicente
V
D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013012:Sorbitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry*
C513881:2,5-dideoxy-2,5-imino-D-glucitol; D000438:Alcohols; D000447:Aldehydes; D004987:Ethers; D011759:Pyrrolidines; D013012:Sorbitol; D014001:Tin; C032519:pyrrolidine